2-(4-methoxyphenyl)-4-methyl-1,3-thiazole-5-carboxylic Acid → HCID 178488950, compound

HRID 1708948Notes

Reaction equation

HRID 1708948 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][C:11]([C:15]([OH:17])=O)=[C:12]([CH3:14])[N:13]=2)=[CH:5][CH:4]=1.[NH2:18][C:19]1[NH:23][N:22]=[N:21][N:20]=1>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][C:11]([C:15]([NH:18][C:19]3[NH:23][N:22]=[N:21][N:20]=3)=[O:17])=[C:12]([CH3:14])[N:13]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 49628432-(4-methoxyphenyl)-4-methyl-1,3-thiazole-5-carboxylic AcidHCID 178509299HCID 178509299, compound

Product 1

HCID 178488950HCID 178488950, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 300 mg (1.20 mmol) of 2-(4-methoxyphenyl)-4-methyl-5-thiazolecarboxylic acid and 292.7 mg (1.81 mmol) of N,N'-carbonyldiimidazole (CDI) in dry dimethylformamide (8 ml) was stirred at room temperature for 1 hour. Under the same conditions, a solution of 5-aminotetrazole (122.8 mg, 1.44 mmol) in dry dimethylformamide (1 ml) was added thereto and allowed to react at 70° C. for 3 hours. After the solvent was distilled off from the reaction mixture, the residue was treated with water under ice-cooling and acidified with 2N-HCl to pH 2. The produced solids were filtered with suction, suspended in 100 ml of water and made alkaline with 1N potassium hydroxide (pH=11). After the impurities were removed from the alkaline solution by extracting with ethyl acetate, the aqueous phase was acidified with 2N-HCl to pH 2 and the deposited solids were filtered with suction, washed with water and recrystallized from methanol-THF-water to give 244.4 mg (yield 64 %) of 2-(4-methoxyphenyl)-4-methyl-N-(1H-tetrazole-5-yl)-5-thiazolecarboxamide as white crystals, m.p. 275°-278° C.

Workup

  1. customto react at 70° C. for 3 hours
  2. distillationAfter the solvent was distilled off from the reaction mixture
  3. additionthe residue was treated with water under ice-
  4. temperaturecooling
  5. filtrationThe produced solids were filtered with suction
  6. customAfter the impurities were removed from the alkaline solution
  7. extractionby extracting with ethyl acetate
  8. filtrationthe deposited solids were filtered with suction
  9. washwashed with water
  10. customrecrystallized from methanol-THF-water

Sources & evidence

ORD record
ord-ee992df448cd4136963e668c668097cf
Source dataset
uspto-grants-1990_08
Patent number
US04946855

Reaction notes

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